“Success is not final, failure is not fatal; it is the courage to continue that counts.”

The White Sox's winter was a lot of things, but above all it was an admission of defeat. It was the organization saying, after years of grasping for wins and for a small hope of contention, that maybe this wasn’t the best way to go about it.

The success or failure of the 2017 edition of the White Sox won’t be judged by wins or losses, but by continuing along the path they started with the winter’s trading of Chris Sale and Adam Eaton. Barring all of the new prospects arriving and hitting their 90th percentile projections (e.g. Lucas Giolito, Reynaldo Lopez, and Yoan Moncada are all basically stars immediately), Jose Quintana, Jose Abreu, and others are going to be following Sale and Eaton out the door. It’s a matter of when, not if.

And yet, 2017 will be memorable for being a clear shift from one era of the franchise to the next. From 2000-2008, the White Sox managed to be quite successful, averaging more than 86 wins per season, finishing below .500 only once, with three playoff appearances, and of course one World Series victory. Kenny Williams demonstrated that in an era when free agent starting pitchers were a poor investment, he could acquire solid no. 2 and no. 3 starters in trades, usually for prospects. Freddy Garcia, Bartolo Colon, Javier Vazquez, and Jose Contreras all joined the homegrown Mark Buehrle and Jon Garland, usually for prospects who did not pan out.

Williams also augmented his roster with mid-level or bargain-bin free agents like Tadahito Iguchi, A.J. Pierzynski, and Jermaine Dye. But that became harder and harder to sustain. Which brings us out of the World Series/Kenny Williams period to 2009-2016, when it became The Drought. The White Sox kept trying to repeat the same formula which had largely worked, building around a solid rotation and patching holes with cheap additions. Unfortunately, the stopgaps got cheaper and cheaper, and worse and worse—from solid role players like Iguchi to vortexes of depression like Jerry Sands.

Budget limitations seemed stuck in the pre-drought era as well, with no White Sox payroll exceeding that of the 2011 club despite revenues exploding league-wide since then. And so, despite the low-cost excellence of Sale, Quintana, Eaton, and Abreu the White Sox couldn’t overcome the back half of their rosters and have now failed to make the playoffs since that 2008 squad squeaked in—the third longest active drought in the league.

For the most part, even for those who were following more closely than would be healthy, the seasons blend together but for the more remarkable failures. The year Adam Dunn inexplicably forgot how to play baseball to a stunning degree was 2011. The year they blew a division lead in humiliating fashion was 2012. The year when the clubhouse melted down over the omnipresence of a 14-year-old boy and the team’s best player eviscerating some throwback jerseys was 2016.

Since 2008, only the 2012 team really made the playoff race interesting. There were some fantastic individual performances, paired with more than enough inadequacy to cancel it out. So, other than some superficial changes, the plan was largely the same and it yielded the same sub par results. For better or for worse, the White Sox are trying a new plan, and what’s startling about that is just how long it has been since they have changed course.

Sure, before now there have been seasons in which the White Sox lost a ton of games like a rebuilding team—2007, 2011, 2013—but none of those years were intended to be rebuilding years. As alluded to above, the 2011 team represents the most they’ve ever invested in payroll and they were definitely going for it. "It" just … imploded. The White Sox certainly thought they were contenders heading into 2013, having just lost the division by three games the year before and bringing back most of the same roster. Again it just … imploded. And whatever selling the 2013 White Sox did was tepid, as Alex Rios and Jake Peavy were traded, but the team would only consider deals with teams that would pay all or most of their salaries, diminishing what they would receive in talent.

Between skimping on drafting, a Latin America program run by a con man, and refusing to ever rebuild to any degree other than what was forced upon them, the White Sox have relentlessly attempted to white-knuckle every team just over the line and into the playoffs, with increasingly poor results. The scope of the change in plan is to finally break away from the organization’s core philosophy that has ruled since the late 90s. For the first time in decades, the plan is built around the hope that the youth now spread out across the minor-league affiliates will one day find success in Chicago.

There’s Moncada, the toolsy, athletic second baseman with power and speed who is surely destined for multiple All-Star appearances and MVP contention.There’s Giolito, the mammoth right-hander with a tempting curveball. There’s Lopez and Michael Kopech, the flame-throwing arms who are hopefully starters but, at worst, a lights out bullpen tandem—or perhaps a cartoonishly potent bullpen if they join Carson Fulmer, Zach Burdi, and Alec Hansen back there. And there’s Zach Collins, who hits moonshots and is maybe not a catcher but let’s see if he can catch because it’d be really cool if he can catch.

That’s the hope, anyway.

Not all of these guys will be hits. Some may wind up traded again down the road if and when the White Sox see another opportunity at contention. But the point of all of this, what will really make this year memorable, is that the path toward contention has changed. After years of trying the same thing over and over again with no success, this year’s White Sox are like Sisyphus finally getting sick of pushing that damn boulder up the hill, getting a jackhammer, and turning that sucker into rubble.

The other point of this is to see it through to culmination. There’s no guarantee that the White Sox, and maybe more specifically their 81-year-old owner Jerry Reinsdorf, won’t cut bait on this long-term makeover at the first whiff of success and speed things up in a detrimental fashion. If the White Sox see this through in trades of Quintana, Todd Frazier, David Robertson, and others—and they’ve given no indication they’ll do anything to the contrary—this year will be remembered for that, regardless of what kind of success they find in the future as a result.

But if this is truly the start of the team turning the table from era to era, from mediocrity to actually building toward something meaningful, this season will be remembered as the opening move in that journey. And while all plans are, in some way, predicated on hope, this year marks a very substantial change in the nature of that hope. Years from now we can continue to debate whether it was a good idea or not, but regardless of how it works out it's difficult to imagine that this year does not mark a sea change for the franchise.

Collin Whitchurch and Nick Schaefer are the co-editors-in-chief of BP South Side.

True! I suppose that would fall under a Rebuilding Type trade (veteran for prospect). For purposes of this article, that occurred in 1998, prior to Kenny Williams taking the helm. So in a sense, in terms of timing and what the organization's philosophy was and when, it still fits.
Very fair point, though.

We should give baseball's "middle class" more respect. The CWS saw a chance to be competitive and took it rather than throwing in the towel. If some of their trades (Samardzija?) and/or prospects (Gordon Beckham?) had worked out better they may have had a few more playoff appearances. From a strategic perspective I find these almost-competitive teams to be the most interesting. Who would want to see a system in which maybe 10 teams compete every year and the rest are in a tear-down mode?

The 2015-16 White Sox were trying to win and wound up being decidedly uninteresting, with the exception of their hot start in 2016. 84-88 win teams are "interesting" for being kind of in the playoff mix. Sub-.500 teams that play like garbage for the majority of the season don't really move the needle.

I have to ask since this is second time BPSS has listed "worst case" or "everything goes wrong" scenarios for at least Kopech & Lopez that they become "lights out in bullpen" or makeup a bullpen that's "one of best in the league", how exactly is that "worst case"? Were that to be the outcome they would at least provide very valuable trade pieces to jump-start rebuild 2.0. I don't think I'm being overly cynical in thinking that the actual and very-possible worst case scenarios for any of these SP prospects is that for one reason or another they don't make it out of minors and/or provide zero value, on-field in Chicago or by trade to Sox. Just seems a bit unrealistic to expect the floor for these SP prospects to become ace relievers dominating the league.

I guess "worst case" isn't the best term to use--along those lines, ask our prospect team how they feel about the word "ceiling."
But in terms of "reasonable worst case" or "likely downside," they project to be very good relievers. Otherwise you're talking about something significant changing about them. Either injury or their stuff backing up.
And unless you have a reason to believe that will happen, then you're just operating from the perspective of, "Well he's a pitcher so he could get hurt and be terrible." And since that's true of everyone, it gets very tiresome to say that over and over again.
Lopez already showed that his stuff can work in the majors last year. Kopech is a bit further away, but he dominated major leaguers in a 2 inning burst against the Cubs just the other day.
But if Lopez, Kopech, Fulmer, and Hansen don't wind up as starters, add those to Nate Jones and Burdi and I don't think it's a stretch to say based on what we know now that should be a really good group.